Trifluoroacetic acid → Ethyl 4-(2-oxo-1,4-dihydropyrido[4,3-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

HRID 493608

Reaction equation

HRID 493608 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1)=O)(C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O>ClCCl>[O:12]=[C:13]1[NH:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[CH2:22][N:23]1[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 682631,1'-CarbonyldiimidazoleHCID 22293255Ethyl 4-[(4-[(tert-butoxycarbonyl)amino]pyridin-3-yl methyl)amino]piperidine-1-carboxylate

Product 1

HCID 22293216Ethyl 4-(2-oxo-1,4-dihydropyrido[4,3-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylateYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.50 mL) was a add to a solution of the material from Step A (0.24 g, 0.63 mmol) in dichloromethane (5 mL). After stirring overnight, another 0.5 mL of trifluoroacetic acid was added. After an additional 2 h, the reaction was concentrated. This material was dissolved in acetonitrile (5 mL) and carbonyldiimidazole (0.31 g, 1.89 mmol) was added at room temperature. After 2 h, the acetonitrile was evaporated in vacuo, the residue partitioned between 1N NaOH and dichloromethane, and the organic phase dried over magnesium sulfate. The crude product was purified by chromatography (silica gel, 10 to 15% methanol in methylene chloride gradient elution), which gave the title compound (0.089 g). MS 305.3.

Workup

  1. waitAfter an additional 2 h
  2. concentrationthe reaction was concentrated
  3. dissolutionThis material was dissolved in acetonitrile (5 mL)
  4. waitAfter 2 h
  5. customthe acetonitrile was evaporated in vacuo
  6. customthe residue partitioned between 1N NaOH and dichloromethane
  7. dry with materialthe organic phase dried over magnesium sulfate
  8. customThe crude product was purified by chromatography (silica gel, 10 to 15% methanol in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-b6a5a596187446ac824723c86497849d
Source dataset
uspto-grants-2009_05
Patent number
US07534784B2

Linked notes

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